1,2-Dioxin
Chemical compound / From Wikipedia, the free encyclopedia
1,2-Dioxin is a heterocyclic, organic, antiaromatic[1] compound with the chemical formula C4H4O2. It is an isomeric form of 1,4-dioxin (or p-dioxin).
Quick Facts Names, Identifiers ...
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Names | |||
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Preferred IUPAC name
1,2-Dioxine | |||
Systematic IUPAC name
1,2-Dioxacyclohexa-3,5-diene | |||
Identifiers | |||
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3D model (JSmol) |
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PubChem CID |
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Properties | |||
C4H4O2 | |||
Molar mass | 84.074 g·mol−1 | ||
Related compounds | |||
Related compounds |
Dibenzodioxin | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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For other dioxin compounds, see dioxin.
Due to its peroxide-like characteristics, 1,2-dioxin is very unstable and has not been isolated. Calculations suggest that it would isomerize rapidly into but-2-enedial.[2] Even substituted derivatives are very labile, e.g. 1,4-diphenyl-2,3-benzodioxin.[3] Indeed, in 1990, 3,6-bis(p-tolyl)-1,2-dioxin was wrongly accounted as the first stable derivative.[4] It was subsequently shown that the initial compound was not a derivative of 1,2-dioxin, but a thermodynamically more stable dione.[5]
- The isomers 1,2-dioxin (left) and 1,4-dioxin (right)
- Structure of the transient 1,4-diphenyl- 2,3-benzodioxin
- Dioxin (1) and dione form (2)